Lily Sky is a former dancer at the Vanilla Unicorn and currently does unpaid work at the parking lot for Jordan Steele. Lily Sky is a free spirit individual who tries to fit in but people truly admire her.
Lily comes from a small sunny and swampy town in Florida. On Lily's 18th birthday, she ran away from home because of an abusive 6-year relationship and her parents trying to force her to adopt their religion after finding her to be bisexual. Lily ran away to Los Santos to live on her own where she met the Li Brothers, Han Li and Jason Li, who offered for her to stay with them along with her best friend Ember. She entered a relationship with Han Li, who also dragged Lily into the life of a criminal. Lily began to feel bad about all the crime she was doing and went in search of redemption.
Redemption from Crime
Lily meets a clown named Mr. Jinglesworth who was a therapist at the Parson Rehabilitation Center. Mr. Jinglesworth took Lily under his wing and taught her the way of a therapist. She was soon employed by the state to give therapy. Lily soon realized how bad Han was for her and, after meeting and spending time with the Chief of Police S.W. Chocolate, she leaves Han for him. Lily finally felt like life was going well until she met a man named Samuel Summerbridge. In her meeting with this man, she learns very quickly that this man is a danger not only to herself but to others, especially her clients. He told Lily it was his obligation to the earth to rid the world of bad people or in his words “free troubled souls”. Samuel ended up kidnapping and torturing Lily until she gave up the names of her clients and friends. Lily was so scared for her life and those around her she gave up therapy and her dream of going down a better path.
Lily was stalked by Samuel and others he paid to follow her around. She became so paranoid that she asked Han for protection since Chocolate was always working. Because of this Chocolate became furious and turned Lily over to Samuel. When Samuel picked up Lily and Chocolate, he stated that it was Chocolate who turned her over and then says people like Chocolate he hates the most. He then shot Chocolate and stabbed Lily in the back.
Lily woke up in the hospital next to Chocolate and, because of her kind heart (or stupidity), chose to give Chocolate a chance because she knows everyone makes mistakes and that there was still good in his heart. When her adopted family and friends found out, they were angry with her so she ended up choosing Chocolate over them. A few months later, Lily was pregnant with twins and soon after became engaged to Chocolate. They began to fight a lot and both agreed to end the relationship. Chocolate took the ending of the relationship very differently from Lily though. Chocolate texted her asking to talk, and when she showed up, he told her that if he can't have her or the kids then no one can. He proceeded to shoot Lily in the stomach, load her into his car, and jump off a building with her in the car. Three lives were lost that day.
Lily moved to a new city to escape Samuel's grasp and the memory of Chocolate. She took up a life of crime again just to get by and in turn meets her now adoptive father Vincent Rosetti, a mob boss who wanted to help her by keeping her away from a criminal life. Lily became a bit bored, so she started traveling just to meet new people. While in another city, she met the love of her life Jayce Adams and things began going well again.
Lily ends up moving again to another city where she found herself around amazing friends that truly admired her personality. Lily started saving and made plans on opening up a coffee shop where you can not only get coffee but play with kittens or even talk to a therapist. Soon after, Lily became pregnant during the economy crash, leaving Lily without money and not knowing what to do. She decided to start working for her friend Candy Moist at the Vanilla Unicorn as an exotic dancer against Jayce's request not to. Lily kept this a secret from Jayce for some time until she was struck by a car and forced to have their child prematurely. While at the hospital, she also found out her mother had died of cancer. Feeling guilty and overwhelmed, Lily told Jayce what she has been doing and Jayce ended the relationship. Lily, feeling not worth anything, decides she is not fit to be a good mother and says goodbye to her beautiful daughter Lilyann.
Having lost faith in living a legal life, Lily realized that being a criminal is what she does best. Lily doesn't hate that she enjoys it but just doesn't care anymore. Lily met Nancy Flutterbottom, who works at the Yellow Jack, and she took Lily under her wing to teach her how to be a smart criminal.